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Favorite
    Exceptional! 5/5
    (17 reviews)
    avg/night
    17
    Favorite
      Excellent! 4.7/5
      (11 reviews)
      avg/night
      11
      Favorite
        Exceptional! 5/5
        (6 reviews)
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        6
        Favorite
          Excellent! 4.7/5
          (6 reviews)
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          6
          Favorite
            Wonderful! 4.8/5
            (23 reviews)
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            23
            Favorite
              Exceptional! 5/5
              (6 reviews)
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              6
              Favorite
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                2
                Favorite
                  Very Good! 4.2/5
                  (5 reviews)
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                  5
                  Favorite
                    Exceptional! 5/5
                    (6 reviews)
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                    6
                    Favorite
                      Excellent! 4.6/5
                      (5 reviews)
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                      5
                      Favorite
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                        1
                        Favorite
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                          1
                          Favorite
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                            Favorite
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                              Favorite
                                Wonderful! 4.9/5
                                (40 reviews)
                                avg/night
                                40
                                Favorite
                                  Very Good! 4.2/5
                                  (5 reviews)
                                  avg/night
                                  5
                                  Favorite
                                    Wonderful! 4.9/5
                                    (14 reviews)
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                                    14
                                    Favorite
                                      Wonderful! 4.9/5
                                      (21 reviews)
                                      avg/night
                                      21
                                      Favorite
                                        Wonderful! 4.9/5
                                        (28 reviews)
                                        avg/night
                                        28
                                        Favorite
                                          Wonderful! 4.9/5
                                          (18 reviews)
                                          avg/night
                                          18
                                          Favorite
                                            Wonderful! 4.9/5
                                            (7 reviews)
                                            avg/night
                                            7
                                            Favorite
                                              Wonderful! 4.8/5
                                              (38 reviews)
                                              avg/night
                                              38
                                              Favorite
                                                Exceptional! 5/5
                                                (6 reviews)
                                                avg/night
                                                6
                                                Favorite
                                                  Wonderful! 4.9/5
                                                  (34 reviews)
                                                  avg/night
                                                  34
                                                  Favorite
                                                    Wonderful! 4.9/5
                                                    (40 reviews)
                                                    avg/night
                                                    40
                                                    Favorite
                                                      Excellent! 4.6/5
                                                      (28 reviews)
                                                      $83
                                                      avg/night
                                                      28
                                                      Favorite
                                                        Wonderful! 4.9/5
                                                        (23 reviews)
                                                        avg/night
                                                        23
                                                        Favorite
                                                          Wonderful! 4.8/5
                                                          (16 reviews)
                                                          avg/night
                                                          16
                                                          Favorite
                                                            Wonderful! 4.9/5
                                                            (23 reviews)
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                                                            23
                                                            Favorite
                                                              Wonderful! 4.9/5
                                                              (19 reviews)
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                                                              19
                                                              Favorite
                                                                Very Good! 4.1/5
                                                                (15 reviews)
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                                                                15
                                                                Favorite
                                                                  Excellent! 4.7/5
                                                                  (21 reviews)
                                                                  avg/night
                                                                  21
                                                                  Favorite
                                                                    Wonderful! 4.8/5
                                                                    (32 reviews)
                                                                    avg/night
                                                                    32
                                                                    Favorite
                                                                      Exceptional! 5/5
                                                                      (19 reviews)
                                                                      avg/night
                                                                      19
                                                                      Favorite
                                                                        Wonderful! 4.8/5
                                                                        (6 reviews)
                                                                        avg/night
                                                                        6
                                                                        Favorite
                                                                          Exceptional! 5/5
                                                                          (9 reviews)
                                                                          avg/night
                                                                          9
                                                                          Favorite
                                                                            Excellent! 4.7/5
                                                                            (21 reviews)
                                                                            avg/night
                                                                            21
                                                                            Favorite
                                                                              Excellent! 4.7/5
                                                                              (27 reviews)
                                                                              avg/night
                                                                              27
                                                                              Favorite
                                                                                Excellent! 4.7/5
                                                                                (7 reviews)
                                                                                avg/night
                                                                                7
                                                                                Favorite
                                                                                  Excellent! 4.6/5
                                                                                  (32 reviews)
                                                                                  avg/night
                                                                                  32
                                                                                  Favorite
                                                                                    Wonderful! 4.8/5
                                                                                    (38 reviews)
                                                                                    avg/night
                                                                                    38
                                                                                    Favorite
                                                                                      Wonderful! 4.8/5
                                                                                      (33 reviews)
                                                                                      avg/night
                                                                                      33
                                                                                      Favorite
                                                                                        Exceptional! 5/5
                                                                                        (16 reviews)
                                                                                        avg/night
                                                                                        16
                                                                                        Favorite
                                                                                          Excellent! 4.6/5
                                                                                          (16 reviews)
                                                                                          avg/night
                                                                                          16
                                                                                          Favorite
                                                                                            Excellent! 4.7/5
                                                                                            (7 reviews)
                                                                                            $97
                                                                                            avg/night
                                                                                            7
                                                                                            Favorite
                                                                                              Wonderful! 4.9/5
                                                                                              (34 reviews)
                                                                                              avg/night
                                                                                              34
                                                                                              Favorite
                                                                                                Wonderful! 4.9/5
                                                                                                (11 reviews)
                                                                                                avg/night
                                                                                                11
                                                                                                Favorite
                                                                                                  Wonderful! 4.9/5
                                                                                                  (14 reviews)
                                                                                                  avg/night
                                                                                                  14
                                                                                                  Favorite
                                                                                                    Exceptional! 5/5
                                                                                                    (8 reviews)
                                                                                                    avg/night
                                                                                                    8
                                                                                                    Favorite
                                                                                                      Wonderful! 4.9/5
                                                                                                      (28 reviews)
                                                                                                      avg/night
                                                                                                      28
                                                                                                       

                                                                                                      Recent Canaan Reviews

                                                                                                      Amazing stay in the Berksires

                                                                                                      5 of 5
                                                                                                      I was looking for a very special place in the Bershires to celebrate my husband's birthday. When I came across The Playhouse my first reaction was, "This is it!" We spent 3 wonderful days enjoying this amazing property and surrounding towns nestled beneath the mountains. The house is impeccably restored to its original splendor with contemporary furnishings and atmosphere that is deserving of a feature in Architectural Digest. We decided to eat most of our meals in to soak up every moment in the unforgettable ambiance. We loved the openess, with great views of the mountains at all times of day. The Sonos sound system really added to the experience. There was just two of us, but with a larger group this house couldn't be more perfect. We really enjoyed the scenic walk past Lake Laurel. The kitchen was amazingly equipped and the entire house from top to bottom was very clean and crisp. The exercise nook downstairs was a nice touch, too. Can't say enough about The Playhouse. Thank you Daniel for sharing this treasure!
                                                                                                      • Submitted: Oct 19, 2017
                                                                                                      • Stayed: Oct 2017

                                                                                                      Just what we needed- Serenity

                                                                                                      5 of 5
                                                                                                      Book this house in any and all seasons. Living in Brooklyn and working in Manhattan may be the dream for many, but it's hard living. We needed some peace and quiet. We chose to stay here and never regretted the decision. The house is an absolute dream. It has mid century charm as well as all of the modern conveniences and luxuries. Heated marble floors, a 2 person spa tub, large 4k TV and more. The front, screened, porch has 4 comfortable seats and reading light. Two of the seats are slide/rockers and the others are large Adirondack chairs. I would recommend you bring a couple camping fold chairs with you. The lake offers beautiful views of wildlife and provides a great deal of privacy. While the water levels were too low to kayak in the section behind the house this week, the other section is ideal. In other seasons or different years you will likely be able to put the kayak or canoe in the water just behind the deck. Perhaps one day they will install a small dock/walkway to aid in this. Even without I would recommend this to anyone looking for a large home and peace. The location is simple amazing for any guests, regardless of their agenda. We were there for leaf peeping(peak week!) and to re-live a trip we took 20 years earlier as teenagers. Activities nearby: The lake house is minutes from Jiminy Peak ski resort(all seasons activities) other ski options Tanglewood music venue(world class) Mount Greylock and dozens of other hikes for all abilities Fishing Biking Hunting Antiques Excellent live theater Very good food Close to Bennington VT (or drive a little more for Brattleboro. It's worth it!) Lenox, Great Barrington, Williamstown and more destinations to visit for Berkshire charm. Outlet shopping at Lee Target is 5 mins away for food or other needs at the house. The kitchen in the house is outstanding! I can go on and on about the wonderful home David and his wife have created. It is warm, inviting and fills you with a sense of peace. Ending each day there will create memories you will cherish for years. Note: if you are not an outdoors person, prepare yourself. This isn't a suburban lifestyle. The home is modern and clean but you are IN nature. You will see animals and insects on your journey. Live with nature, don't fight it. **Also be mindful that a very sweet cat lives in the nearby home and sometimes can be seen near the Rambling stream or waterfall that runs parallel to the driveway. Please drive slow to protect our friend
                                                                                                      • Submitted: Oct 16, 2017
                                                                                                      • Stayed: Oct 2017